Hydroxylamine → 2-(4-{[2-(Hydroxyamino)-5-pyrimidin-2-ylpentyl]sulfonyl}piperazin-1-yl)-5-(2,2,2-trifluoroethoxy)pyrimidine

HRID 1723807Notes

Reaction equation

HRID 1723807 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[CH:23][N:22]=2)[CH2:17][CH2:16]1)(=[O:14])=[O:13].[NH2:33][OH:34].[NH4+].[Cl-]>C1COCC1>[OH:34][NH:33][CH:10]([CH2:9][CH2:8][CH2:7][C:2]1[N:1]=[CH:6][CH:5]=[CH:4][N:3]=1)[CH2:11][S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:22]=[CH:23][C:24]([O:27][CH2:28][C:29]([F:30])([F:31])[F:32])=[CH:25][N:26]=2)[CH2:17][CH2:16]1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 25517Ammonium ChlorideHCID 688456502-(4-{[(1E)-5-pyrimidin-2-ylpent-1-en-1-yl]sulfonyl}piperazin-1-yl)-5-(2,2,2-trifluoroethoxy)pyrimidine

Product 1

HCID 866145742-(4-{[2-(Hydroxyamino)-5-pyrimidin-2-ylpentyl]sulfonyl}piperazin-1-yl)-5-(2,2,2-trifluoroethoxy)pyrimidineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(4-{[(1E)-5-pyrimidin-2-ylpent-1-en-1-yl]sulfonyl}piperazin-1-yl)-5-(2,2,2-trifluoroethoxy)pyrimidine (8.79 g, 18.6 mmol) in THF (90 mL) was added 50% aqueous solution of hydroxylamine (18 mL) and the reaction stirred at room temperature for 2 hours. A saturated solution of NH4Cl (200 mL) was then added and then this was extracted twice with extracted with EtOAc (2×250 mL), combined organics washed with brine (250 mL), dried (MgSO4), filtered and concentrated in vacuo to give 2-(4-{[2-(hydroxyamino)-5-pyrimidin-2-ylpentyl]sulfonyl}piperazin-1-yl)-5-(2,2,2-trifluoroethoxy)pyrimidine as a pale yellow solid (8.96 g, 17.7 mmol, 95%).

Workup

  1. extractionthis was extracted twice
  2. extractionwith extracted with EtOAc (2×250 mL)
  3. washcombined organics washed with brine (250 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dce9c566431b416087edc8e33afef6d7
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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